


The One Where Sam Wears Panties

by sixtysevenlmpala



Category: Supernatural
Genre: Blow Jobs, Caught, Crossdressing Kink, Discovery, First Time, M/M, Masturbation, Panty Kink, Tumblr Prompt, Weecest, Weechesters
Language: English
Status: Completed
Published: 2013-06-13
Updated: 2013-06-13
Packaged: 2017-12-14 21:13:28
Rating: Explicit
Warnings: Underage
Chapters: 1
Words: 2,692
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/841447
Author URL: https://archiveofourown.org/users/sixtysevenlmpala/pseuds/sixtysevenlmpala
Summary: <blockquote class="userstuff">
              <p>Written for <a href="http://rainforever69.tumblr.com/">rainforever69</a>'s prompt: "Weecest where Sam starts crossdressing and then Dean discovers he wears panties and it turns him on like hardcore."<br/>He’s not obsessed or anything, it’s just that he really goddamn loves the feeling of them, caressing his ass and cradling his dick in soft lace, so maybe, maybe he buys a few more pairs. Okay, maybe it’s a pair every new place they stay.<br/>Originally posted on <a href="http://sixtysevenlmpala.tumblr.com/post/51481872086/the-first-time-a-pair-catches-sams-eye-hes">tumblr</a>.</p>
            </blockquote>





	The One Where Sam Wears Panties

The first time a pair catches Sam’s eye, he’s thirteen, and [they’re](http://www.lasenza.co.uk/media/catalog/product/cache/2/image/9df78eab33525d08d6e5fb8d27136e95/b/a/base.11020444-59A4.jpg) [black](http://www.lasenza.co.uk/media/catalog/product/cache/2/back_image/9df78eab33525d08d6e5fb8d27136e95/b/a/back.11020444-59A4.jpg). Intricate lace pattern all over with a pretty scalloped edging, and the strip of material at the back is so thin it makes his mouth dry up a little. They’re… well, Sam thinks they’re beautiful. He and Dean are on a rare trip to the mall, in a town where barely anyone even knows their names yet and by the looks of things, they won’t get a chance to before they’re gone again; Dean is over by the fountain chatting up what looks to be three girls, and damn it, Sam can’t stop staring at the mannequin in the window of a lingerie store.

Because it’s wearing those panties, and he wishes he was instead.

It’s a startling desire, one that he knows he’ll have to roll over in his mind and ponder to within an inch of its life at some point, but for now he’s living on borrowed time – Dean’s going to be back any minute with either a slapped face or a phone number scribbled on his palm – so Sam darts inside the store, stutters out some story about how they’re for his girlfriend, pays up, ditches the bag and stuffs them in his pocket.

“Hey, Sammy, ready to skip?” Dean says not a minute later, and Sam turns to see him rubbing at his cheek, a brilliant red hand print already forming there. Sam nods and settles into teasing him about striking out until he pouts and shoves Sam’s shoulder, and Sam just tries to pretend the weight of his purchase in his pocket isn’t there.

He tries them on that night, locked safely in the cramped bathroom of the motel they’re holding up in. He has to stand on his tiptoes to get a good view in the mirror, but when he does, he loses his breath a little. They look a little awkward, sure, _feel_ a little awkward with the way he had to cram his dick into them, but the lace feels like feathers on his skin and they hug his ass in a way that makes him feel special, almost sexy. Like a girl – something to be treasured, taken care of.

A sudden banging on the door makes him jump, jolts him out of his thoughts, and his hands immediately cup over his crotch before he realises he locked the door. “Sam! C’mon, bitch, I don’t got all night!” Dean’s voice filters through, and Sam shivers, wonders what Dean would think of him like this. After a moment’s hesitation, he leaves the panties on, tugs the rest of his clothes on over them.

That night, he doesn’t sleep.

 

***

After that, it kind of becomes a _thing_. He’s not obsessed or anything, it’s just that he really goddamn _loves_ the feeling of them, caressing his ass and cradling his dick in soft lace, so maybe, maybe he buys a few more pairs. Okay, maybe it’s a pair every new place they stay.

Sam builds up quite a collection, eventually. He keeps them all squashed into the bottom of his duffel, snatching it away from Dean if he tries to pack for him or look for something. There are cotton boyshorts that he finds disappointingly, well, boyish; bikini-cut panties with brightly coloured spots that make him feel daring and bold; even a couple of thongs, and those make him feel completely dirty, like a slut in the best possible way; but the lace ones he has the most of, and they’re always his favourite by far, delicate and teasing, exposing just enough of his ass for him to feel sexy as hell.

When he’s just turned fifteen, Sam finds out that if he jerks off wearing a pair of panties – especially the lacy kind – he comes like a freakin’ freight train, harder and faster than he ever has without them. After he makes that particular discovery, getting himself off normally loses its appeal somewhat, just doesn’t compare – but he holds himself back from doing it that way too often; washing them in secret’s a bitch, and anyway, he’s scared he’ll ruin them.

When he does let himself, he makes sure it’s an evening where he’ll be alone, when Dean and their dad have gone out on a hunt and explicitly told him not to expect them back until the next day, or insanely late that night. Then, he’ll lie spread-eagled on his bed, undress himself down to his pretty lacy panties and take his time with it. He’ll play with his nipples until they’re about as hard as his dick, tease himself and make himself gasp for it before he snakes a hand down and rubs himself through the lace, letting it catch on his sensitive skin.

Yeah, tonight is one of those nights.

“Fuck,” Sam whispers, years of keeping quiet while jerking off drummed into him through mortifying experience, and he clamps down hard on his lip with his teeth as he looks down his body, sees his cock stretching the panties out in ways that they shouldn’t be stretched, tenting them with how hard he is. He groans, breaths already coming short, and he slips a hand inside, rearranges himself so that the head of his cock peeks out over the waistband.

[These](http://www.lasenza.co.uk/media/catalog/product/cache/2/image/9df78eab33525d08d6e5fb8d27136e95/b/a/base.122532-017.H60_5_1.jpg.jpg) [panties](http://www.lasenza.co.uk/media/catalog/product/cache/2/back_image/9df78eab33525d08d6e5fb8d27136e95/b/a/back.122532-017.H60_5_1.jpg.jpg) are one of his favourite pairs, and he saves them for nights like this. Lacy white flushing into a bright, hot pink near the top, the cut of the back riding high on his ass cheeks and the delicate lace teasing his cock without him even doing anything. The head of his cock is flushed a dark pink, complimenting his panties, and Sam moans as he lets the waistband scratch at that patch of nerves just under the head.

Hand outside his panties, he rubs his palm up and down his shaft, shuddering as his cock leaks a little onto his belly. He can feel a wet patch already formed under the lace from before he moved his dick, and he lets out another moan, breathy and strained. Panting a little, Sam rolls onto his belly, hand wedged underneath him, and he rocks his hips down into his palm, setting a pace that grows more and more frantic as he works himself up. The friction of the lace on his dick is just the right side of too-much, setting his nerves on fire and forcing him to moan loud and unashamed into the pillow under his face, back arching as he ruts his hips.

As it always does when he’s this turned-on, the image of Dean pops into his head, and he simply doesn’t have the drive to force himself to replace it with something else, something more appropriate. His attraction to Dean has been a problem for years, now, and sometimes he just wants to give himself a break and let himself fantasise for once. After all, it’s only fantasy, right?

His brother’s name falls from his lips on a gasp, and he thinks about Dean’s mouth. It’s a pretty frequent thought of Sam’s in these situations. He imagines him on his knees, flashing Sam that signature cocky grin before just—just burying his face in Sam’s crotch and going to _town_ – shit, maybe licking him through his panties ‘til Sam’s shivering with sensitivity, and then he’d tug them down, tuck them under his balls and wrap those plump lips around his cock—

“Dean, Dean, Dean,” Sam chanted breathlessly, hips juddering into his own palm, eyes screwed shut as he loses himself in his own mind, and he guesses that’s why he doesn’t hear the door until it slams shut and a taken aback voice says, “Sammy?”

Sam’s heart stops, and he looks over his shoulder abruptly to see Dean – actual Dean, not fantasy Dean, fuck fuck _fuck fuck fuck fuck_ – standing by the door and staring over to where he must have a perfect view of his little brother, humping his own hand, wearing pink and white lacy panties. Awesome.

“Dean, I. I.” Sam stalls, completely at a loss. His hand is still _pressed against his dick,_ he’s still lying there looking over his shoulder, Dean’s still standing there utterly gobsmacked.

“Uh. Dad, uh… sent me back. What are you—“ Dean begins, walking cautiously towards him, eyes wide as saucers.

“Please don’t tell Dad,” Sam blurts, and as Dean gets even closer, he scrambles further up the bed, his face burning with humiliation. He draws his knees up, puts his arms around them and sits facing Dean, eyeing him warily and trying to suppress a stupid urge to cry.

Dean smiles a little crookedly. “Why would I tell…?” he trails off, shaking his head like Sam’s being silly. “Jesus Christ, Sam,” he mutters hoarsely, and Sam wants to shrivel up and die because he’s staring, his eyes are roaming over Sam’s thighs and his chest and his stomach and, yeah, his panties, as much as he’s trying to obscure them from view. It’s a look that Sam might even call _hungry_ , like he’s drinking him in, but he knows that’s just wishful thinking and the fact that his cock is still half-hard making him think that. Dean licks his lips and says quietly, “You were saying my name.”

“Shut up,” Sam whispers, looking away, lip trembling. “Just… just leave it, okay, Dean?” and he rolls off the bed on the opposite side to the one his brother’s sitting on, marching straight to the bathroom and locking the door. He leans his back against the door and slowly slides down to the floor, burying his face in his hands. He refuses to cry. He’s _not_ going to cry.

Knock-knock-knock. “Sam?” Dean calls.

“I said leave it,” Sam mumbles miserably, and he hears Dean sigh.

“Will you just let me talk? God _damn_.”

Sam sniffles. “Fine.”

There’s a pause, and Dean says, “So, panties, huh?”

Sam groans. “Shut up. I mean it.”

Another sigh, this one harsher, more frustrated. “Look, do you… do you even know how hot you look?” Sam’s head shoots up, his breath catching. He wonders if he even heard what he thought he just did.

“Don’t… don’t fuck with me,” he whispers.

“I’m not,” Dean protests, and Sam swallows thickly. “Sammy, look, I’m. I’m not angry, and I’m not gonna tell Dad, and I’m not freaked out, or whatever the hell else is goin’ through that little head right now. I think you look good.”

Sam’s heart pounds against his chest. “Yeah?”

“Fuck, yeah.” Dean’s voice is rough, gravelly like Sam’s never heard it before, and his stomach rolls with anticipation, excitement and wariness all rolled into one. “I mean, damn, kiddo, anyone with eyes would think the same. You’re… God, you look _pretty._ So beautiful in your little panties. Fuck. God. I never even… never imagined anythin’ like it, Sammy.”

“D’you mean it?” Sam asks shakily, standing now and facing the door.

“Why don’t’cha let me in an’ I’ll show you how much I mean it,” Dean mutters, his voice dark and slow and full of promise, and Sam’s fingers _shake_ as he fumbles with the lock.

As soon as it’s open, Dean pushes through, hands immediately going for Sam’s hips as he bends his neck down to kiss him. Sam’s completely caught off-guard, gasping into Dean’s mouth, and he can practically _taste_ Dean’s smirk as he slips his tongue into Sam’s now-open mouth, hands sliding around to squeeze at Sam’s ass, and God, _God_ his fingers catch on the lace and grind it into his ass as he grabs him and it’s all so much.

Sam moans, cock hardening again so fast it’s dizzying, and Dean chuckles when his hips jerk forward to rut against Dean’s thigh. “Jesus. Look at you. Thought about this, Sammy.” Sam makes a questioning noise, and Dean laughs again. “Okay, not—not _these_ , exactly,” he clarifies, squeezing Sam’s panty-clad ass again and stroking his thumbs over the lace, “but… you, yeah. Wanted you, Sam, I didn’t think you’d—“

“Well, I do,” Sam cuts him off, and Dean huffs out a third laugh. Sam blushes. “Why are you _laughing_?”

“M’happy,” Dean mutters, and without another word, he slams the bathroom door shut and shoves Sam up against it, and goddamn it, he falls to his knees, just like in every single fucking fantasy Sam has ever _had_ about him.

“Oh God,” Sam says, overwhelmed, staring down at his brother with a hand clamped like a vice on his shoulder.

“Y’want this, right?” Dean asks in a serious tone, and his breath washes out hot over Sam’s cock, and Sam’s nodding frantically, having apparently forgotten the art of speech. His cock is just as hard as it was before Dean walked in on him, possibly even more, and he can’t stop shifting his hips even as Dean leans in and presses his mouth to the bulge under the fabric. There’s no cocksure grin flashed up at him, but there’s a long, sultry, sincere look as Dean drags the flat of his tongue right up the shaft of Sam’s cock through the panties, and somehow that’s even hotter. Dean’s tongue is hot and clever, dancing around the head of Sam’s cock where it pokes up over the waistband.

Sam lets out a whine, and Dean laughs, _laughs against his cock_ and the vibration makes him moan, fingernails digging into Dean’s shoulder through his shirt. This is the point in Sam’s well-worn fantasy where Dean would take his cock out of his panties and suck him like a pro, but then Dean’s winking up at him and tucking all of his cock back under the panties, setting it at a diagonal so it fits, and Sam’s momentarily confused before Dean presses his lips to his lace-covered cockhead and _sucks_. “Oh, _shit_ ,” Sam groans, hips pushing forward against Dean’s mouth, and Dean calmly pins his hips to the door.

“Thought you’d like that,” Dean mumbles into his crotch, and then he’s doing it again, but this time he’s not letting up, a constant suction at the head of his cock and occasionally wandering down his shaft. The lace soon turns a darker shade in that whole area, wet with Dean’s spit and Sam’s pre-come. Dean’s messy with it, see, wet and sloppy so that he makes this obscene slurping sound as he sucks, but it only serves to make Sam shudder in his grip, only reminds him of how real this all is. Because Dean is blowing him through his fucking favourite lace panties, and Sam’s about to lose his goddamn mind.

“O-oh my god, I’m gonna,” Sam chokes out, and his cheeks flush even more than they already were because it’s kind of stupidly fast, but he’s teetering right on the edge, and he’s sure anyone in their right mind would forgive him if they saw Dean like this.

“C’mon, then,” Dean mutters, sucking hard at the head of his cock through the lace, “go on an’ make a mess in your pretty panties, Sammy,” and Sam throws his head back and comes, hips straining against Dean’s grip as he spurts inside the delicate material, Dean moaning right along with him, tongue darting out to lap up the taste.

After Sam comes down, he’s oddly oversensitive, the cling of wet lace around his cock too much for him to stand without his legs trembling a little, knees threatening to buckle. Dean seems to get it even though Sam can only whimper, and he gently peels them off, licks Sam’s cock clean with careful kitten licks until Sam pushes weakly at his forehead. “Holy crap,” Sam exhales after a while, and Dean leans his forehead against his hip and laughs.

“C’mere,” Dean says.

Sam slides down the door until he hits the floor, then tugs a still-kneeling Dean down on top of him for a slow, messy kiss. Taking a breath, Sam trails his hand down to Dean’s crotch, raising his eyebrows when he finds him hard and straining against his zipper. “So, panties, huh?” Sam teases, echoing Dean’s words from earlier, and Dean shrugs an agreement and kisses him again.

**Author's Note:**

> Thanks for reading, feel free to leave a comment/kudos if you liked!


End file.
